SYNTHESIS OF ANOMERIC SPIRO URACIL NUCLEOSIDES WITH AN ORTHOESTER STRUCTURE - STEREOSELECTIVE CYCLIZATION CONTROLLED BY THE C6-SUBSTITUENT

Authors
KITTAKA A TANAKA H KATO H NONAKA Y NAKAMURA KT MIYASAKA T
Citation
A. Kittaka et al., SYNTHESIS OF ANOMERIC SPIRO URACIL NUCLEOSIDES WITH AN ORTHOESTER STRUCTURE - STEREOSELECTIVE CYCLIZATION CONTROLLED BY THE C6-SUBSTITUENT, Tetrahedron letters, 38(36), 1997, pp. 6421-6424
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
36
Year of publication
1997
Pages
6421 - 6424
Database
ISI
SICI code
0040-4039(1997)38:36<6421:SOASUN>2.0.ZU;2-I
Abstract
Uracil nucleosides having an anomeric orthoester structure were synthe sized fi om 2'-deoxy-6-(hydroxyalkyl)uridines through hypoiodite-initi ated cyclization. The hydroxyalkyl substituent at the 6-position was f ound to control the anomeric stereochemistry (beta/alpha=7/1 similar t o 1/46) of the cyclization. The transition state geometry of the react ion was postulated based on the X-ray crystallographic structure of th e cyclized product 7 alpha to elucidate the observed stereoselectivity . (C) 1997 Elsevier Science Ltd.